Eschweiler-Clarke反应

  • A+

   伯、仲胺用甲醛/甲酸体系还原甲基化。由于N-甲基是许多环状生物碱的结构特征，因此，该反应常用于生物碱的合成。




反应机理


氨与甲醛通过一个缩醛胺中间体形成席夫碱，甲酸上的氢负离子转移到亚胺得到相应的N-甲基胺，如果原料胺为伯胺，则重复前面步骤。




反应实例







参考文献


1. Eschweiler, W. Ber. 1905, 38, 880-887.

2. Clarke, H. T., Gillespie, H. B., Weisshaus, S. Z. J. Am. Chem. Soc. 1933, 55, 4571-4587.

3. Martinez, A. G., Vilar, E. T., Fraile, A. G., Ruiz, P. M., San Antonio, R. M., Alcazar, M. P. M. Tetrahedron: Asymmetry 1999, 10, 1499-1505.

4. Smith, A. B., III, Friestad, G. K., Barbosa, J., Bertounesque, E., Duan, J. J. W., Hull, K. G., Iwashima, M., Qiu, Y., Spoors, P. G., Salvatore, B. A. J. Am. Chem. Soc. 1999, 121, 10478-10486.

5. Lakshmaiah, G., Kawabata, T., Shang, M., Fuji, K. J. Org. Chem. 1999, 64, 1699-1704.

6. Argouarch, G., Gibson, C. L., Stones, G., Sherrington, D. C. Tetrahedron Lett. 2002, 43, 3795-3798.


摘自：有机人名反应——机理及应用 第四版，Strategic Applications of Named Reactions in Organic Synthesis


weinxin
我的微信
关注我了解更多内容

发表评论

目前评论：4

    • grainly 2022年10月13日 20时05分 [value:no/]层

      Our first experiment demonstrated that injection of TAM intraperitoneal, or ICI into the lateral ventricle, deactivated MPN MOP and facilitated lordosis in EB primed rats lasix to torsemide conversion In the following Q A story, Wilmot

      • admisoT 2022年12月31日 02时52分 [value:no/]层

        Setting Women s Hospital Prof cialis online without prescription com 20 E2 AD 90 20Cat 20Costa 20O 20Pastila 20Viagra 20In 20Farmacii 20 20Generic 20Viagra 20Vancouver generic viagra vancouver Houston Rockets There are justifiable doubts as to whether Dwight Howard is still worth the massive contract and star status after enduring back problems and spoiling two franchises

        • Inderve 2023年11月17日 00时36分 [value:no/]层

          More Study Monitoring Needed buy cialis online cheap 286, 297, 100 S

          • Jinaivy 2024年08月26日 10时08分 [value:no/]层

            CONSORT diagram with predicted numbers of participants at each stage of the trial priligy 30mg tablets Survival and tumour characteristics of breast cancer patients with germline mutations of BRCA1